HRP20150229T1 - Spojevi heteroarila kao ligandi receptora 5-ht4 - Google Patents
Spojevi heteroarila kao ligandi receptora 5-ht4 Download PDFInfo
- Publication number
- HRP20150229T1 HRP20150229T1 HRP20150229AT HRP20150229T HRP20150229T1 HR P20150229 T1 HRP20150229 T1 HR P20150229T1 HR P20150229A T HRP20150229A T HR P20150229AT HR P20150229 T HRP20150229 T HR P20150229T HR P20150229 T1 HRP20150229 T1 HR P20150229T1
- Authority
- HR
- Croatia
- Prior art keywords
- oxadiazol
- piperidin
- chloro
- ylamine
- chroman
- Prior art date
Links
- 108091005482 5-HT4 receptors Proteins 0.000 title claims 4
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- SVIPNSAZTOJNPK-UHFFFAOYSA-N 2-(1-cyclobutylpiperidin-4-yl)-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1C1CCC1 SVIPNSAZTOJNPK-UHFFFAOYSA-N 0.000 claims 1
- ZCLZOGZSLISYIY-UHFFFAOYSA-N 2-(1-cyclopentylpiperidin-4-yl)-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1C1CCCC1 ZCLZOGZSLISYIY-UHFFFAOYSA-N 0.000 claims 1
- JTRVNNILEYAXKB-UHFFFAOYSA-N 2-(1-cyclopropylpiperidin-4-yl)-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1C1CC1 JTRVNNILEYAXKB-UHFFFAOYSA-N 0.000 claims 1
- HUYJRMFAFYNTRY-UHFFFAOYSA-N 2-(1-propan-2-ylindazol-3-yl)-5-(1-propan-2-ylpiperidin-4-yl)-1,3,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1C1=NN=C(C=2C3=CC=CC=C3N(C(C)C)N=2)O1 HUYJRMFAFYNTRY-UHFFFAOYSA-N 0.000 claims 1
- RZQYGOMRYRZHLD-UHFFFAOYSA-N 2-(3-cyclobutyl-3-azabicyclo[3.1.0]hexan-6-yl)-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(C1C2)C1CN2C1CCC1 RZQYGOMRYRZHLD-UHFFFAOYSA-N 0.000 claims 1
- SOPKFQVZINHHEW-LREBCSMRSA-N 2-[(1-cyclobutylpiperidin-4-yl)methyl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1CC(CC1)CCN1C1CCC1 SOPKFQVZINHHEW-LREBCSMRSA-N 0.000 claims 1
- JBVWUUUWTXYKGV-UHFFFAOYSA-N 2-[(1-cyclobutylpiperidin-4-yl)methyl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1CC(CC1)CCN1C1CCC1 JBVWUUUWTXYKGV-UHFFFAOYSA-N 0.000 claims 1
- OBQZRZCCOLRCKJ-UHFFFAOYSA-N 2-[1-(2-methoxyethyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C1CN(CCOC)CCC1C1=NN=C(C=2C3=CC=CC=C3N(C(C)C)N=2)O1 OBQZRZCCOLRCKJ-UHFFFAOYSA-N 0.000 claims 1
- XHXCJKNEBFAUSE-UHFFFAOYSA-N 2-[1-(3-methoxypropyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCCOC)CCC1C1=NN=C(C=2C3=CC=CC=C3N(C(C)C)N=2)O1 XHXCJKNEBFAUSE-UHFFFAOYSA-N 0.000 claims 1
- MTHISTWFYBPNHH-UHFFFAOYSA-N 2-[1-(3-methylbutyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C1CN(CCC(C)C)CCC1C1=NN=C(C=2C3=CC=CC=C3N(C(C)C)N=2)O1 MTHISTWFYBPNHH-UHFFFAOYSA-N 0.000 claims 1
- LVIZUKFRUKBLEZ-UHFFFAOYSA-N 2-[1-(cyclobutylmethyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1CC1CCC1 LVIZUKFRUKBLEZ-UHFFFAOYSA-N 0.000 claims 1
- QZTKHUMXLKMPFW-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1CC1CC1 QZTKHUMXLKMPFW-UHFFFAOYSA-N 0.000 claims 1
- NFGIGHUJZHKVGT-UHFFFAOYSA-N 2-[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2C(C3=NN=C(O3)C3C4C3CN(C4)CCCOC)=NN(C(C)C)C2=C1 NFGIGHUJZHKVGT-UHFFFAOYSA-N 0.000 claims 1
- MWQFEYAZEZGUFA-UHFFFAOYSA-N 2-[3-(cyclobutylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(C1C2)C1CN2CC1CCC1 MWQFEYAZEZGUFA-UHFFFAOYSA-N 0.000 claims 1
- VOWXDOMJEFCEAC-UHFFFAOYSA-N 2-[3-(cyclopropylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole;oxalic acid Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(C1C2)C1CN2CC1CC1 VOWXDOMJEFCEAC-UHFFFAOYSA-N 0.000 claims 1
- ZVPZZDDNJCMQAG-UHFFFAOYSA-N 5-chloro-7-[5-(1-cyclobutylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1-benzofuran-4-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(Cl)C(N)=C2CCOC2=C1C(O1)=NN=C1C(CC1)CCN1C1CCC1 ZVPZZDDNJCMQAG-UHFFFAOYSA-N 0.000 claims 1
- IOAUUAHBJZZZAS-UHFFFAOYSA-N 5-chloro-7-[5-(1-cyclopropylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1-benzofuran-4-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(Cl)C(N)=C2CCOC2=C1C(O1)=NN=C1C(CC1)CCN1C1CC1 IOAUUAHBJZZZAS-UHFFFAOYSA-N 0.000 claims 1
- KILDCHBCPPPOJP-UHFFFAOYSA-N 5-chloro-7-[5-[1-(oxan-4-ylmethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1-benzofuran-4-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(Cl)C(N)=C2CCOC2=C1C(O1)=NN=C1C(CC1)CCN1CC1CCOCC1 KILDCHBCPPPOJP-UHFFFAOYSA-N 0.000 claims 1
- ABRLWSBQYFGGMJ-UHFFFAOYSA-N 6-chloro-8-[5-(1-cyclobutylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine Chemical compound C1=2OCCOC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CCC1 ABRLWSBQYFGGMJ-UHFFFAOYSA-N 0.000 claims 1
- JXDHEGNLQLKXOB-UHFFFAOYSA-N 6-chloro-8-[5-(1-cyclobutylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CCC1 JXDHEGNLQLKXOB-UHFFFAOYSA-N 0.000 claims 1
- UUTZBLPMKADLIH-UHFFFAOYSA-N 6-chloro-8-[5-(1-cyclopentylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CCCC1 UUTZBLPMKADLIH-UHFFFAOYSA-N 0.000 claims 1
- FOSWJADTAFUWAW-UHFFFAOYSA-N 6-chloro-8-[5-(1-cyclopropylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCOC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CC1 FOSWJADTAFUWAW-UHFFFAOYSA-N 0.000 claims 1
- JJJUWKQTDCNZKZ-UHFFFAOYSA-N 6-chloro-8-[5-(1-cyclopropylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CC1 JJJUWKQTDCNZKZ-UHFFFAOYSA-N 0.000 claims 1
- JLQUCYAMLNLIIN-UHFFFAOYSA-N 6-chloro-8-[5-(1-propan-2-ylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1CN(C(C)C)CCC1C1=NN=C(C=2C=3OCCCC=3C(N)=C(Cl)C=2)O1 JLQUCYAMLNLIIN-UHFFFAOYSA-N 0.000 claims 1
- OGKPCEKQRYMOMQ-UHFFFAOYSA-N 6-chloro-8-[5-(2-piperidin-1-ylethyl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1CCN1CCCCC1 OGKPCEKQRYMOMQ-UHFFFAOYSA-N 0.000 claims 1
- NWRXGIDJWLLMBG-UHFFFAOYSA-N 6-chloro-8-[5-(3-cyclobutyl-3-azabicyclo[3.1.0]hexan-6-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(C1C2)C1CN2C1CCC1 NWRXGIDJWLLMBG-UHFFFAOYSA-N 0.000 claims 1
- MGOCDTKKNFKTFJ-UHFFFAOYSA-N 6-chloro-8-[5-(3-piperidin-1-ylpropyl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1CCCN1CCCCC1 MGOCDTKKNFKTFJ-UHFFFAOYSA-N 0.000 claims 1
- JQXRUYUXBCUEMQ-UHFFFAOYSA-N 6-chloro-8-[5-(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-6-yl)-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1CCOC2=C1C(N)=C(Cl)C=C2C(O1)=NN=C1C1C2C1CN(C(C)C)C2 JQXRUYUXBCUEMQ-UHFFFAOYSA-N 0.000 claims 1
- ATYKXMXTFKDVKE-UHFFFAOYSA-N 6-chloro-8-[5-[(1-cyclobutylpiperidin-4-yl)methyl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1CC(CC1)CCN1C1CCC1 ATYKXMXTFKDVKE-UHFFFAOYSA-N 0.000 claims 1
- SDZLJWUMDIDUFS-UHFFFAOYSA-N 6-chloro-8-[5-[(1-cyclopentylpiperidin-4-yl)methyl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1CC(CC1)CCN1C1CCCC1 SDZLJWUMDIDUFS-UHFFFAOYSA-N 0.000 claims 1
- GTUCZTYJFXBSTJ-UHFFFAOYSA-N 6-chloro-8-[5-[1-(2-methoxyethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1CN(CCOC)CCC1C1=NN=C(C=2C=3OCCCC=3C(N)=C(Cl)C=2)O1 GTUCZTYJFXBSTJ-UHFFFAOYSA-N 0.000 claims 1
- MOCJXOLSHILLJW-UHFFFAOYSA-N 6-chloro-8-[5-[1-(3-methoxypropyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(CCCOC)CCC1C1=NN=C(C=2C=3OCCOC=3C(N)=C(Cl)C=2)O1 MOCJXOLSHILLJW-UHFFFAOYSA-N 0.000 claims 1
- PSXYGKNEXSPUHC-UHFFFAOYSA-N 6-chloro-8-[5-[1-(3-methoxypropyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1CN(CCCOC)CCC1C1=NN=C(C=2C=3OCCCC=3C(N)=C(Cl)C=2)O1 PSXYGKNEXSPUHC-UHFFFAOYSA-N 0.000 claims 1
- MPDKVUXWJYUTJG-UHFFFAOYSA-N 6-chloro-8-[5-[1-(3-methylbutyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1CN(CCC(C)C)CCC1C1=NN=C(C=2C=3OCCCC=3C(N)=C(Cl)C=2)O1 MPDKVUXWJYUTJG-UHFFFAOYSA-N 0.000 claims 1
- IKDXVSAZYALSJB-UHFFFAOYSA-N 6-chloro-8-[5-[1-(cyclobutylmethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine Chemical compound C1=2OCCOC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1CC1CCC1 IKDXVSAZYALSJB-UHFFFAOYSA-N 0.000 claims 1
- JRCYLOFVFYSPRU-UHFFFAOYSA-N 6-chloro-8-[5-[1-(cyclopropylmethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1CC1CC1 JRCYLOFVFYSPRU-UHFFFAOYSA-N 0.000 claims 1
- YGQJRLOVIBEEMG-UHFFFAOYSA-N 6-chloro-8-[5-[1-(oxan-4-yl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCOC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CCOCC1 YGQJRLOVIBEEMG-UHFFFAOYSA-N 0.000 claims 1
- ASHAZFNSXQEWEL-UHFFFAOYSA-N 6-chloro-8-[5-[1-(oxan-4-yl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1C1CCOCC1 ASHAZFNSXQEWEL-UHFFFAOYSA-N 0.000 claims 1
- NPRWNKJAJXITKC-UHFFFAOYSA-N 6-chloro-8-[5-[1-(oxan-4-ylmethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-2,3-dihydro-1,4-benzodioxin-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCOC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1CC1CCOCC1 NPRWNKJAJXITKC-UHFFFAOYSA-N 0.000 claims 1
- YRZAONSGNIZSEC-UHFFFAOYSA-N 6-chloro-8-[5-[1-(oxan-4-ylmethyl)piperidin-4-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(CC1)CCN1CC1CCOCC1 YRZAONSGNIZSEC-UHFFFAOYSA-N 0.000 claims 1
- AFBCUMPEIQDFJT-UHFFFAOYSA-N 6-chloro-8-[5-[3-(cyclobutylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(C1C2)C1CN2CC1CCC1 AFBCUMPEIQDFJT-UHFFFAOYSA-N 0.000 claims 1
- PHBJHQYYMLWCFH-UHFFFAOYSA-N 6-chloro-8-[5-[3-(cyclopropylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]-1,3,4-oxadiazol-2-yl]-3,4-dihydro-2h-chromen-5-amine Chemical compound C1=2OCCCC=2C(N)=C(Cl)C=C1C(O1)=NN=C1C(C1C2)C1CN2CC1CC1 PHBJHQYYMLWCFH-UHFFFAOYSA-N 0.000 claims 1
- -1 amen oxalate salt Chemical class 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- FYAKAOSUPUZQTC-UHFFFAOYSA-N ethyl 4-[4-[5-(4-amino-5-chloro-2,3-dihydro-1-benzofuran-7-yl)-1,3,4-oxadiazol-2-yl]piperidin-1-yl]piperidine-1-carboxylate;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C(=O)OCC)CCC1N1CCC(C=2OC(=NN=2)C=2C=3OCCC=3C(N)=C(Cl)C=2)CC1 FYAKAOSUPUZQTC-UHFFFAOYSA-N 0.000 claims 1
- XVKQBWCBEZSBDM-UHFFFAOYSA-N ethyl 4-[4-[5-(5-amino-6-chloro-3,4-dihydro-2h-chromen-8-yl)-1,3,4-oxadiazol-2-yl]piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1CCC(C=2OC(=NN=2)C=2C=3OCCCC=3C(N)=C(Cl)C=2)CC1 XVKQBWCBEZSBDM-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- YDQDIKYQYPYXMY-UHFFFAOYSA-N oxalic acid;2-(2-piperidin-1-ylethyl)-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1CCN1CCCCC1 YDQDIKYQYPYXMY-UHFFFAOYSA-N 0.000 claims 1
- XYLACSFPOYMLLD-UHFFFAOYSA-N oxalic acid;2-[1-(oxan-4-yl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1C1CCOCC1 XYLACSFPOYMLLD-UHFFFAOYSA-N 0.000 claims 1
- YTGJXFMVMWXTCY-UHFFFAOYSA-N oxalic acid;2-[1-(oxan-4-ylmethyl)piperidin-4-yl]-5-(1-propan-2-ylindazol-3-yl)-1,3,4-oxadiazole Chemical compound OC(=O)C(O)=O.C12=CC=CC=C2N(C(C)C)N=C1C(O1)=NN=C1C(CC1)CCN1CC1CCOCC1 YTGJXFMVMWXTCY-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Claims (9)
1. Spoj opće formule (I):
[image]
u kojem
[image]
je
[image]
[image]
je
[image]
[image]
je točka spajanja;
R1 je alkil, R3-O-R3 ili
[image]
R2 je cikloalkil ili heterociklil, i opcionalno supstituiran vodikom, alkilom ili sa -CO-OR3;
R3 je alkil;
"Y" je C ili O;
"m" je cijeli broj u rasponu od 0 do 1; s time da kad m=0, onda je R1 cikloalkil ili heterociklil;
"n" je cijeli broj u rasponu od 0 do 2;
"p" je cijeli broj u rasponu od 0 do 1; ili neka njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, izabran iz skupine koju sačinjavaju:
6-Kloro-8-[5-(1-ciklopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin hemi fumarat;
6-Kloro-8-[5-(1-ciklobutil piperdin-4-ilmetil)-[1,3,4]oksadiazol-2-il]-kroman-5-il mine L(+)-tartarat sol;
6-Kloro-8-[5-(1-ciklobutil piperdin-4-ilmetil)-[1,3,4]oksadiazol-2-il]-kroman-5-il amin;
1-Izopropil-3-{5-[1-(3-metoksipropil)piperidin-4-il]-[1,3,4]oksadiazol-2-il}-1H-indazol oksalat sol;
3-[5-(1-Ciklobutil-piperidin-4-il metil)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol L(+)-tartarat sol;
6-Kloro-8-[5-(3-ciklobutil-3-aza biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]kroman-5-ilamin oksalat sol;
4-[5-(8-Amino-7-kloro-2,3-dihidrobenzo[1,4]dioksan-5-il)-[1,3,4]oksadiazol-2-il]-[1,4’]bipiperidinil-1’-karboksilna kiselina etil ester oksalat sol;
5-Kloro-7-{5-[1-(tetrahidropiran-4-il)piperidin-4-il]-[1,3,4]oksadiazol-2-il}-2,3-dihidro, benzofuran-4-il amin
oksalat sol;
6-Kloro-8-{5-[1-(2-metoksi-etil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-kroman-5-ilamin;
6-Kloro-8-{5-[1-(3-metil-butil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-kroman-5-ilamin;
6-Kloro-8-[5-(1,-ciklobutilmetil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-[5-(1-ciklopropilmetil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-[5-(1-izopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-{5-[1-(3-methoksi-propil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-kroman-5-ilamin;
6-Kloro-8-[5-(1-ciklobutil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-[5-(1-ciklobutilmetil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-2,3-dihidro-benzo[1,4]dioksin-5-ilamin;
6-Kloro-8-[5-(1-ciklobutil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-2,3-dihidro-benzo[1,4]dioksin-5-ilamin;
6-Kloro-8-[5-(1-ciklopentil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-[5-(2-piperidin-1-il-etil)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
4-[5-(5-Amino-6-kloro-kroman-8-il)-[1,3,4]oksadiazol-2-il]-[1,4’]bipiperidinil-1’-karboksilna kiselina etil ester;
6-Kloro-8-[5-(3-piperidin-1-il-propil)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-[5-(1-ciklopentil-piperidin-4-ilmetil)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin oksalat sol;
6-Kloro-8-[5-(3-izopropil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin oksalat sol;
6-Kloro-8-[5-(3-ciklobutilmetil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin oksalat sol;
6-Kloro-8-[5-(3-ciklopropilmetil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-kroman-5-ilamin;
6-Kloro-8-{5-[1-(tetrahidro-piran-4-il)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-kroman-5-ilamin oksalat sol;
6-Kloro-8-{5-[1-(tetrahidro-piran-4-ilmetil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-kroman-5-ilamin oksalat sol;
5-Kloro-7-[5-(1-ciklopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-2,3-dihidro-benzofuran-4-ilamin oksalat sol;
5-Kloro-7-[5-(1-ciklobutil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-2,3-dihidro-benzofuran-4-ilamin oksalat sol;
6-Kloro-8-[5-(1-ciklopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-2,3-dihidro-benzo[1,4]dioksin-5-ilamin oksalat sol;
6-Kloro-8-{5-[1-(tetrahidro-piran-4-il)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-2,3-dihidro-benzo[1,4]dioksin-5-ilamin oksalat sol;
6-Kloro-8-{5-[1-(3-methoksi-propil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-2,3-dihidro-benzo[1,4]dioksin-5-ilamin oksalat sol;
6-Kloro-8-{5-[1-(tetrahidro-piran-4-ilmetil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-2,3-dihidro-benzo[1,4]dioksin-5-ilamin oksalat sol;
5-Kloro-7-{5-[1-(tetrahidro-piran-4-ilmetil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-2,3-dihidro-benzofuran-4-ilamin oksalat;
4-[5-(4-Amino-5-kloro-2,3-dihidro-benzofuran-7-il)-[1,3,4]oksadiazol-2-il]-[1,4’]bipiperidinil-1’-carboksilic acid etil ester oksalat;
3-[5-(1-Ciklobutilmetil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol;
1-Izopropil-3-{5-[1-(2-metoksi-etil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-1H-indazol;
3-[5-(1-Ciklobutil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol;
1-Izopropil-3-[5-(1-izopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1H-indazol;
3-[5-(1-Ciklopropilmetil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1 H-indazol;
1-Izopropil-3-{5-[1-(3-metil-butil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-1H-indazol;
3-[5-(1-Ciklopropil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol;
3-[5-(1-Ciklopentil-piperidin-4-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol;
1-Izopropil-3-{5-[3-(3-metoksi-propil)-3-aza-biciklo[3.1.0]heks-6-il]-[1,3,4]oksadiazol-2-il}-1H-indazol oksalat sol;
3-[5-(3-Ciklobutil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol oksalat salt;
3-[5-(3-Ciklobutilmetil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol oksalat sol;
3-[5-(3-Ciklopropilmetil-3-aza-biciklo[3.1.0]heks-6-il)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol oksalat sol;
1-Izopropil-3-{5-[1-(tetrahidro-piran-4-ilmetil)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-1 H-indazol oksalat sol;
1-Izopropil-3-{5-[1-(tetrahidro-piran-4-il)-piperidin-4-il]-[1,3,4]oksadiazol-2-il}-1 H-indazol oksalat sol;
1-Izopropil-3-[5-(2-piperidin-1-il-etil)-[1,3,4]oksadiazol-2-il]-1H-indazol oksalat sol i
3-[5-(1-ciklobutil piperidin-4-il metil)-[1,3,4]oksadiazol-2-il]-1-izopropil-1H-indazol oksalat sol;
ili njihove farmaceutski prihvatljive soli.
3. Postupak pripreme spoja čija je formula (I) prema zahtjevu 1, koji uključuje:
(a) spajanje spoja formule (1) sa spojem formule (2)
[image]
u prisutnosti sredstva za dehidraciju da bi se dobio spoj formule (I), pri čemu su sve supstitucije one definirane u zahtjevu 1,
(b) opcionalno konvertiranje spoja formule (I) u njegove farmaceutski prihvatljive soli.
4. Postupak pripreme spoja čija je formula (I) prema zahtjevu 1, koji uključuje:
(a) spajanje spoja formule (1) sa spojem formule (2)
[image]
u prisutnosti prikladnog otapala da bi se dobio spoj formule (4),
[image]
(b) cikliranje spoja formule (4) da bi se dobio spoj formule (I), pri čemu su sve supstitucije one definirane u zahtjevu 1,
(c) opcionalno konvertiranje spoja formule (I) u njegove farmaceutski prihvatljive soli.
5. Farmaceutski pripravak koji sadrži neki spoj u skladu s bilo kojim od zahtjeva 1 do 2 i farmaceutski prihvatljive pomoćne tvari.
6. Farmaceutski spoj u skladu sa zahtjevom 5, za liječenje kliničkih stanja posredovanih preko receptora 5-HT4 kao što su poremećaj nedostatka pažnje i hiperaktivnosti, alzheimerova bolest, kognitivni poremećaji, demencija ili shizofrenija.
7. Spoj prema bilo kojem od zahtjeva 1 do 2 za primjenu u liječenju bolesti vezanih uz receptore 5-HT4.
8. Spoj prema zahtjevu 7, za primjenu u liječenju kliničkih stanja kao što su poremećaj nedostatka pažnje i hiperaktivnosti, alzheimerova bolest, kognitivni poremećaji, demencija ili shizofrenija.
9. Spoj formule (I) prema zahtjevu 1 ili zahtjevu 2, za primjenu u liječenju nekog poremećaja središnjeg živčanog sustava koji je povezan s receptorima 5-HT4 ili pod njihovim utjecajem.
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| EP12716662.7A EP2758394B1 (en) | 2011-09-19 | 2012-01-05 | Heteroaryl compounds as 5-ht4 receptor ligands |
| PCT/IN2012/000011 WO2013042135A1 (en) | 2011-09-19 | 2012-01-05 | Heteroaryl compounds as 5-ht4 receptor ligands |
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| JP2016523813A (ja) * | 2013-04-05 | 2016-08-12 | エービーシー バイオサイエンス エーエス | 医学的使用、特に酸化ストレスまたは炎症に関連する疾患の治療、および臓器の保存または洗浄のための、バレッチンおよびその誘導体 |
| NZ720879A (en) | 2013-12-16 | 2017-05-26 | Suven Life Sciences Ltd | Indazole compounds as 5-ht4 receptor agonists |
| AP2017009755A0 (en) | 2014-08-16 | 2017-02-28 | Suven Life Sciences Ltd | Process for large scale production of 1-isopropyl-3-{5-[1-(3-methoxypropyl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-1h-indazole oxalate |
| EP3265459B1 (en) * | 2015-02-13 | 2019-05-15 | Suven Life Sciences Limited | Amide compounds as 5-ht4 receptor agonists |
| CN107540568A (zh) * | 2017-08-25 | 2018-01-05 | 许昌恒生制药有限公司 | 一种乙氧酰胺苯甲酯的制备方法 |
| MA53918A (fr) * | 2018-10-18 | 2022-01-26 | Suven Life Sciences Ltd | Nouvelles utilisations d'un agoniste du récepteur 5-ht4 |
| CN114502540A (zh) | 2019-05-31 | 2022-05-13 | 医肯纳肿瘤学公司 | Tead抑制剂和其用途 |
| CN110746450A (zh) * | 2019-09-17 | 2020-02-04 | 济南康和医药科技有限公司 | 一种贝前列素钠关键中间体的合成方法 |
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| JPH06509574A (ja) * | 1991-08-03 | 1994-10-27 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５−ｈｔ↓４レセプターアンタゴニスト |
| TW360653B (en) * | 1995-03-01 | 1999-06-11 | Janssen Pharmaceutica Nv | A oxadiazole compound having colon motility stimulating properties, its preparation process and its pharmaceutical composition |
| EP0863897B1 (fr) * | 1995-11-09 | 1999-06-16 | Synthelabo | Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h)-one, utiles comme ligands des recepteurs 5-ht4 ou h3 |
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| CA2545092C (en) | 2003-11-24 | 2010-08-17 | Pfizer Inc. | Quinolonecarboxylic acid compounds having 5-ht4 receptor agonistic activity |
| EA012615B1 (ru) | 2005-02-22 | 2009-10-30 | Пфайзер Инк. | Производные оксииндола в качестве агонистов 5-htрецептора |
| EP1856114B1 (en) | 2005-02-25 | 2014-08-20 | Pfizer Inc. | Benzisoxazole derivatives |
| ES2333545T3 (es) | 2005-07-22 | 2010-02-23 | Pfizer, Inc. | Derivados de indazolcarboxamida como agonistas de receptores 5ht4. |
| KR101121240B1 (ko) * | 2005-12-23 | 2012-06-12 | 에프. 호프만-라 로슈 아게 | 아릴-아이속사졸-4-일-옥사다이아졸 유도체 |
| US20080167286A1 (en) * | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| US20080255203A1 (en) * | 2007-04-12 | 2008-10-16 | Abbott Laboratories | Heterocyclic compounds and their methods of use |
| JP5656880B2 (ja) * | 2009-03-09 | 2015-01-21 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | Ｐｉ３キナーゼの阻害剤としての４−オキサジアゾール−２−イル−インダゾール |
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2015
- 2015-02-26 HR HRP20150229AT patent/HRP20150229T1/hr unknown
- 2015-03-30 CY CY20151100308T patent/CY1116173T1/el unknown
- 2015-04-09 SM SM201500087T patent/SMT201500087B/xx unknown
- 2015-06-10 US US14/735,237 patent/US9636335B2/en active Active
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